Diisopropylethylamine → (S)-6-(2-Hydroxy-2-methyl-propyl)-6-phenyl-3-((S)-1-{4-[1-((S)-tetrahydro-furan-2-carbonyl)-piperidin-4-yl]-phenyl}-ethyl)-[1,3]oxazinan-2-one

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Reaction Steps

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (125 mg) was added to a solution of (S)-tetrahydro-furan-2-carboxylic acid (45 mg) and diisopropylethyl-amine (200 μL) in N,N-dimethylformamide (2 mL) at room temperature. The resulting solution was stirred for 30 min, before (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one (150 mg) dissolved in dimethylformamide (1 mL) was added. The resulting solution was stirred at room temperature overnight and then concentrated under reduced pressure. The crude product was purified by HPLC on reversed phase (MeCN/H2O/NH3) to afford the title compound.

Provenance & Evidence